The Greatest star Jaalen Best has no illusions about being like Muhammad Ali. But after spending the better part of four years immersed in the world of the legendary boxer for Prime Video’s new series, the relative newcomer delivers a towering, eerily authentic performance that feels like the makings of a star—even as he works off-screen to untangle where Ali ends and he begins.
Created by Cross showrunner Ben Watkins and executive produced by Michael B. Jordan and Jay-Z, The Greatest is the first authorized scripted series from Ali’s estate. The eight-episode first season, which debuts November 4, chronicles a young Cassius Clay’s rise from his 1960 Olympic gold medal win in Rome to his 1964 heavyweight championship fight against Sonny Liston and his subsequent name change to Muhammad Ali.
Outside the ring, the story is largely set in Louisville, Kentucky, where Ali’s newfound fame is met with racist Jim Crow laws. As he prepares for his professional debut, Ali leans on the tough love of his tight-knit family: his father Cassius Clay Sr. (Omari Hardwick); mother Odessa “Bird” Clay (Dana Gourrier); and younger brother Rudy (Kai Parham), who would later take the name Rahaman Ali. The final result is as much a coming-of-age tale as it is a classic family drama.
“When I was younger, I knew of Muhammad Ali, and I knew that he was a great boxer, but that was as far as it went,” Best tells Teen Vogue in his first major one-on-one interview about the highly anticipated series. “Being young, especially, you’re not in a position to understand how great someone is, especially outside of the athletic realm, [and] what they sacrificed. But this role allowed me to deep dive and dissect this great man outside of just a boxer.”
Courtesy of Prime Video
Unearthing a fresh perspective on a figure as thoroughly documented as Ali is no small feat. The global cultural icon has been immortalized in numerous books, documentaries, and films, including the 2001 Oscar-nominated biopic starring Will Smith and 1977’s The Greatest, in which Ali played himself. Watkins was initially reluctant to spearhead the project, daunted by the challenge of doing justice to his own childhood hero. But once Jordan convinced him to sign on as showrunner, Watkins was committed to bringing something new to the story.
As Watkins points out, most people already picture Ali as a “fully formed hero.” “I decided I was going to disconnect people from that hero and show them the young man who would one day become that hero, who was a kid with a lot of vulnerabilities and frailties,” he says. “I also made the decision that we will always be looking for the moments in between the things we’ve seen: the moments after the documentary cameras went off, the moments after the arena lights went off.”
The prospect of retracing Ali’s “road to greatness” was particularly appealing to his widow, Lonnie Ali, who has been fiercely protective of his legacy for over four decades, especially in the 10 years since his death. Toward the end of his life, her husband “was always concerned about connecting to the next generation,” young people who never saw him fight live or had the chance to meet him, Lonnie Ali tells Teen Vogue. He worried about what would come after he was gone: “Would those young people remember him? Would they want to know about him?”
Today, Lonnie believes her late husband’s spirit and legacy remain “as strong as ever,” and his example speaks to the present moment. In her view, the way he lived offers a path forward for everyone: how to live as neighbors, how to treat one another with compassion, and how to move through the world with “courage and conviction.”
Courtesy of Prime Video
With Lonnie on board as an executive producer, Watkins penned a pilot script that convinced Amazon to green-light a full series. Her involvement deepened from there, as she was tasked with reading every script and ensuring that key plot points were grounded in historical accuracy. But the show’s success was always going to hinge on one crucial decision. “I told them, ‘You have to find the right, Muhammad Ali. I don’t know how long it could take,’” says Watkins. “I half-jokingly said, ‘If you don’t find him, we can’t make the show.”
“I was very realistic that I knew we would never have a fully formed version of [Cassius]. Nobody was going to be a turnkey—and I liked that idea,” Watkins adds.
Along with casting director Kim Coleman, Watkins and his creative team spent nearly a year considering hundreds of young Black actors for the coveted title role, scouring local gyms, theater companies and talent agencies. Watkins initially gave Coleman three criteria: a newcomer with an athletic background from the Southeastern United States. What Coleman didn’t know was that Watkins was also looking for someone with some “familial baggage,” since he wanted an actor who could tap into visceral emotions for a coming-of-age story.
Best was perfect. Born in Alexandria, Virginia, he is the second-youngest of five children on his mother’s side and grew up in a packed house, with siblings, cousins, an aunt, and an uncle all under one roof. His family later moved to Clinton, North Carolina, for his grandfather’s military service. Through it all, his mother was his anchor. “I had a very similar background to young Ali—the way I adored my mother, and respected my mother for all the sacrifices she made. I, too, wanted to just improve her life as much as possible,” Best says. But unlike Ali, he never had much of a relationship with his father.
Courtesy of Prime Video
Best is also a self-described “class clown” who often landed in trouble and even got suspended from school, never imagining he’d pursue a career in the arts. He attended East Carolina University, where he earned a bachelor’s degree in exercise physiology, initially planning to work in physical or occupational therapy.
In 2019, Best’s then-girlfriend talked him into auditioning for a local musical production of Pocahontas, where he landed the role of Pocahontas’ father, Chief Powhatan. At the time, he was walking on to the men’s basketball team, which meant four-hour practices followed by an hour-and-a-half drive to a two-hour rehearsal in his hometown. “Doing that pretty much every other day was insane for me,” he recalls. “Because basketball wasn’t turning out the way that I wanted, I ended up quitting and just focusing on the rehearsal.”
Best moved to Los Angeles soon after—a city he had never even visited before—a couple of months after graduating in 2020, at the height of the COVID-19 pandemic. After a year learning the ropes as a background actor, he landed small guest-starring roles on American Horror Stories, All American: Homecoming, and Magnum P.I. But dissatisfied with the roles he was getting, Best parted ways with his agent and took a full year off, during which he auditioned for Juilliard—the world-renowned performing arts conservatory—and was very nearly admitted as a student.
“[That experience] really unlocked something in me to be like, ‘If I make it to the final round callbacks of Juilliard and I went up against all of these people, then I can make it in this industry,’” Best recalls. “That’s what switched everything for me. I just had to surround myself [with] the right team and then believe it for myself.” Within a month of signing with new representation, in May 2023, he landed his first audition for The Greatest.
Best had moved from Los Angeles back home to Alexandria, where he was working a full-time remote job as a camp operations coordinator for the American Diabetes Association. Over the next year, he treated the audition process as a “side quest” alongside his ADA work, trying out six or seven times for the role of Ali. By early 2024, the creative team had whittled the field down to four actors, who faced two final tests: a physical evaluation and a chemistry read.
During the two-day physicality evaluation, Watkins brought the four actors together for a boxing session without telling them they would be meeting one another, wanting to see how they would react to the “threat of competition.” Watkins stayed only briefly, since he “didn’t want them always thinking they’re performing,” leaving a team member posing as a gym employee to observe on both days. That evening, Watkins sent each of the candidates a link to the third round of Ali’s Olympic gold-medal fight. “We asked them to study that fight overnight and then come into the gym with the third round memorized,” he says. The next day, they trained even harder one-on-one with a coach so Watkins could see how they’d perform under exhaustion.
What set Best apart, Watkins says, was a combination of self-assuredness and a voracious appetite for learning. “He was green as an actor, but he was a sponge,” the showrunner says. There was also the matter of resemblance: A boxing trainer remarked that Best’s back, shoulders, and legs were reminiscent of Ali’s, which privately got Watkins thinking about how a young actor with the right frame could grow into the older Ali in future seasons. Finally, there was what Watkins calls Best’s “natural charisma”: the quick smile, the twinkle in his eye. Lonnie recognized something familiar as well, growing visibly emotional as she described how naturally Best captured her late husband’s gait, attire, and kid-friendly nature.
The day after Watkins officially told him he’d landed the part, Best boarded a flight to Louisville, where he met Lonnie for the first time at the Muhammad Ali Center. Lonnie says it felt like meeting the 21-year-old she first knew as a child all over again. “When I first met him, the first thing I had to do was FaceTime Hana,” she says of Ali’s second-youngest daughter, who is the spitting image of him. “I said, ‘Hana’—I put my phone up to Jaalen—‘who is this?’ She looked, and she went, ‘Is he kin to us? He looks like it. Is he a relative?’ I said, ‘No.’ She goes, ‘Is he playing Daddy?’ And I said, ‘Yeah.’ She was like, ‘Oh my God.’”
From the moment he got the Ali family’s seal of approval, Best had just six months to get into tip-top shape. He began training in Los Angeles with boxing coach Rob Salley, who told him he would have to slim down to play a young Cassius. They trained six days a week, three hours a day, with running and a strict diet. Salley also had him break down clips of Ali’s fights, and after months of studying little else, Best began boxing like Ali naturally. The workload didn’t let up once cameras rolled last year in Toronto. “Imagine it’s your first time as a series regular. You’re also number one on the call sheet, which is a crazy amount of pressure, and you’re in most of the scenes, but you’ve got to train on all your downtime,” Watkins says. “In between all those moments, you not only have to train so that your body is the way we need it, but you have to practice all the fights and perfect all the choreography.”
Best chose to focus on the years he would actually be playing in season 1, when Ali was 18 to 22. Still, he went down a rabbit hole of Ali’s interviews, studying his mannerisms, from “how he pats his leg when he’s talking or pats his arm,” to his facial expressions and his habit of looking to the side while speaking. Now, on his first-ever press tour, he has borrowed a few of those habits, answering questions as deliberately as Ali did and bringing some of his playfulness to his own interviews, including this one.
The overlap has left Best still working out the blurring divide between himself and Ali. In mid-January, Best attended a U.S. Postal Service stamp event in Louisville, where he spent time with Ali’s children. That night, he texted Lonnie. “Dang, for once in my life, I feel like it’s more fun playing Ali than it is being Jaalen Best,” he recalls telling her. At 28, he says he hasn’t fully discovered who Jaalen Best is yet, and after nearly four years consumed by this role, he feels he has barely lived his own life. “It does make me wonder if the public is going to get more comfortable with Jaalen through Ali,” he admits, “or do I pull back from that and just find myself a little bit?”
Lonnie has warned Best about the weight of carrying Ali’s legacy. She inherited that mantle herself after his death, and she knows how heavy and all-consuming it is. “I want him to learn from the role, and from what he learns about Muhammad, take away the things that he thinks he identifies with, that he thinks might enrich his life,” Lonnie says of Best. “But for goodness sake, don’t try to be Muhammad in real life because it will consume you. You can’t do it. I wish he could, but it’s too much to ask. I hope people don’t do that to him, but I know they are.”
Watkins has tried to help Best see the role as an opportunity rather than a burden. “That is a choice that you can make,” he says. “If you see there’s an opportunity, that doesn’t mean it’s not an obligation.” He also backed that advice with specific casting choices. During the making of the first season, Watkins intentionally hired older Black men—including Michael Ealy, who plays Malcolm X, and Hardwick—to act as father- or uncle-like figures for Best. “We all understood that our job is not only to help Jaalen do a great performance of Muhammad Ali,” Watkins says, “but to set him up for a long career.”
Best admits he finds the prospect of fame “very exciting.” His biggest fear, though, is losing himself amid the notoriety, especially since this role will almost certainly define the rest of his life.
“I’m constantly around people who allow me to be happy, but they’ll constantly remind me, ‘Yeah, you can’t get tied into fame. You have to enjoy it,’” he says. “Not many people at all, except the ones we know of, get to portray Muhammad Ali and walk in his shoes and see how he thought and what he was made of,” Best says of the opportunity. Rather than shying away from the pressure, he is leaning into it. “I want to feel a little bit of what he experienced, and I think from that, I can find my true self,” he says. “I think I’m playing him to figure out who Jaalen wants to be.”